The Executive Brand Podcast – Details, episodes & analysis

Sydney Sloan was previously the CMO at G2, Drata, and Salesloft, prior to which she spent 16 years at Adobe in a variety of marketing leadership roles. She is currently an advisor at G2 and Executive in Residence at Scale Venture Partners, working with early-stage founders on go-to-market strategy.

In this episode, we talk about her biggest lessons, how buyer behavior has fundamentally changed, why brand matters more than ever, and what the 2026 marketing playbook actually looks like.

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We discuss:

* Why this is the biggest transformation in 30 years of B2B marketing

* Buyer research shifted from 29% to 50% on AI chatbots in 4 months, and what that means for you AEO strategy

* Why you probably don't need marketing automation the way you used to

* “Human in the loop” vs “human in the lead”

* How to build brand in 2026 - and why it matters more than ever

* The Show-Up-Bigger-Than-You-Are playbook

* Reorganizing GTM teams around outcomes, not functions

* The advice Sydney would give herself before her first CMO role

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Connect with Sydney:

* LinkedIn: https://www.linkedin.com/in/sydsloan/

* G2: https://www.g2.com/

* Scale Venture Partners: https://www.scalevp.com/

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Connect with Finn:

* LinkedIn: https://www.linkedin.com/in/finnthormeier/

* Project 33: https://www.project33.io/

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My personal takeaways:

1. The shift to AI search is happening faster than we think. Internal G2 data showed that in April 2025, 29% of buyers said they started their research in of of the AI chatbots. By August that number hit 50%, just four months later. In 2026, every company needs to focus on their AEO strategy making sure their brand is the citation source LLMs use.

2. Marketing automation as we know it is dead. Companies need to capture high-intent signals using tools like Clay or Common Room, and immediately deploy AI agents to act on them. Speed is the new currency.

3. Show up bigger than you are. Sydney got this advice from the CMOs of Okta and Snyk, and used it to scale Drata and Salesloft. You don’t need a massive budget, you need one anchor event or one bold move. At Drata, they bought out every ad space for two blocks around Moscone Center for RSA Conference so attendees couldn’t miss them. At Salesloft, they bought a billboard on Highway 101, but the ROI didn’t come from the traffic driving by, it came from leveraging photos of it online. Big one-off events, if properly leveraged, signal momentum to investors, customers and potential employees.

4. We’re entering the “Rick Rubin Economy”, because AI lowers the barrier to entry for content and code, so the only differentiator is taste. You can’t prompt your way to good taste. We need to hire for context and judgment, or leverage advisory boards of influencers who actually understand the market. AI provides the speed, but humans provide the creative direction that determines if anyone actually cares.

5. Do we need GTM Architects? Everyone is rushing to hire GTM Engineers and build AI workflows, but in software development, you need engineers and architects. They work at different levels of abstraction. Software Engineers build and maintain software, Software Architects design the system as a whole. We need this for GTM. You need someone to map the strategy, choose the agentic platforms, and decide *what* to automate before you build it. Sydney said she sees this as a separate role, likely sitting in RevOps, not something for the CMO.

6. The biggest mistake new CMOs make is obsessing over their domain of the marketing department. Sydney’s advice for someone stepping into a C-level role for the first time: Spend your first 90 days building deep relationships with your peers - the CFO, CRO, CEO. If you don’t understand the business context and have alignment with your peers, the best marketing strategy in the world won’t save you.

Jessica Gilmartin was previously the CMO and CRO at Calendly, Head of Revenue Marketing at Asana, and Head of Product Marketing for Wildfire at Google. Today, she works closely with founders and first-time CMOs from pre-revenue through $100M ARR, advising them on everything from hiring, org design to GTM focus and executive communication.

In this episode, we talk about how AI is changing the CMO role and marketing org, where it’s wildly overhyped vs working, and many other topics.

Listen on: YouTube, Spotify or Apple Podcast

We discuss:

* Why CMO + CRO combo roles usually fail

* Why companies now hire CMOs from smaller, scrappier startups

* Where AI is truly useful vs pure hype

* Why random acts of marketing kill momentum

* How Calendly moved from viral PLG to focused enterprise ABM

* The real reason CMOs only last 18 months

* Why taste, courage, and focus still matter more than tools

Connect with Jessica:

* LinkedIn: https://www.linkedin.com/in/jessicagilmartin/

Connect with Finn:

* LinkedIn: https://www.linkedin.com/in/finnthormeier/

* Project 33: https://www.project33.io/

My personal takeaways:

* We’re overvaluing AI right now: Jessica believes we’ll replace most of our day-to-day work with AI in 5-10 years. But right now board members are mandating AI adoption without specific use cases. The reality is AI is making teams 10-20% more efficient and that it works as an enabler, but not as a replacement. The best use cases she’s seeing are data enrichment for lead prioritization, competitive research for product marketing, and using LLMs as synthetic customer panels.

* There are three paths to CMO and CEOs keep hiring wrong. 50% of B2B CMOs come from product marketing, 50% from demand gen, brand CMOs are rare in B2B. CEOs want a unicorn who’s great at both strategic messaging and technical growth. Jessica’s advice: “It’s like asking a backend engineer why they can’t code mobile apps.” Hire for your actual problem right now, not the one you’ll have at $100M.

* The only mistake with bad hires is keeping them. Jessica repeats this constantly to clients, that you will always make bad hires. Or you hire people who were good then but aren’t right now. The mistake afterwards is keeping them too long. When you bring the right person on board, your life gets 10-100x easier.

* Attribution is broken and that’s okay. You’re getting 70-80% accuracy at best. Jessica’s approach is to use the 80-20 rule. Get directionally correct data so teams understand where they can make impact and then work from there. The bigger issue is that companies wait too long to implement basic data and reporting infrastructure.

* Random acts of marketing kill focus. At Calendly, Jessica pivoted the entire team to one thing: repositioning for enterprise customers. Because their CAC was zero for casual users due to viral growth. Marketers hate focus and they want to sprinkle seeds everywhere. But the winning strategy is making big bets, being explicit about trade-offs, and ensuring no one does random acts of marketing.

Joe Ciarallo led comms at Salesforce, Toast (through IPO), and now Wellhub (formerly Gympass), a $2.4 billion corporate-wellness company.He’s seen what happens when scrappy startup PR turns into an IPO-ready machine.

In this episode, Joe breaks down exactly how to build that engine. From category creation at Salesforce to crisis playbooks at Toast, and how to make your founder’s voice a real strategic asset. What you’ll learn:- How Salesforce invented the “Marketing Cloud.”- The shift from scrappy PR to strategic comms.- The new PR mix: owned + earned.- Where AI fits in comms, and why thought leadership will become more valuable, not less.- How companies like Ryanair earned trust by explaining the logic behind unpopular choices.- Why separating those functions is already outdated.- How Salesforce and Toast decide who shows up, what to say, and why empathy is non-negotiable.- Joe’s rule: just start. Post, iterate, learn, repeat.Perfect for founders who:- Want to look public-ready long before the IPO- Need to balance credibility with control- Are scaling fast and can’t afford to “wing comms” anymore- Believe the founder’s voice is part of the brand- Want to build real authority on LinkedIn without sounding corporate

Connect with Joe:- Joe’s Linkedin: https://www.linkedin.com/in/joeciarallo/- Wellhub: https://wellhub.com/

Connect with me: - LinkedIn: https://www.linkedin.com/in/finnthormeier/- Website: https://www.project33.io/- Podcast: https://open.spotify.com/show/03CXzsZp7wdqIRVDcqPTFH

Chapters00:00 – “Dress for the job you want, even as a startup.”01:20 – The Salesforce Marketing Cloud story05:50 – How owned + earned media play off each other08:30 – The rise of podcasts as the new PR11:40 – Turning scrappy PR into an IPO-ready function14:00 – How Toast prepped for IPO16:15 – AI, content, and speed18:20 – Why AI can’t create thought leadership20:30 – The new transparency: explaining the why22:00 – When journalists check your LinkedIn25:50 – Internal vs external comms is outdated30:00 – The rise of the Chief Comms Officer32:00 – Coaching founders to lead industries, not just products34:00 – Crisis playbooks and empathy36:00 – Why comms leaders should post too38:10 – CEO visibility and leading by example40:00 – Wrap-up

Cobi Blumenfeld-Gantz is the CEO and Co-founder at Chapter, a technology-driven Medicare advisor improving how seniors choose their health coverage.

How do you reduce the time spent on founder-led sales? This is one of many topics I covered in my conversation with Cobi Blumenfeld Gantz.

In this episode, we are talking about:

- Why the Founder Should Drive Your Marketing

- How to Reduce the Time Spent on Founder-Led Sales

- The Big Problem in the Medicare Industry

- How 90% of Partners Get Referrals Working With Chapter

Cobi Linkedin: https://www.linkedin.com/in/cobibgantz/

Chapter: https://askchapter.org/

Podcast: https://open.spotify.com/show/03CXzsZp7wdqIRVDcqPTFH

LinkedIn: https://www.linkedin.com/in/finnthormeier/

Website: https://www.project33.io/

#linkedin #founderledmarketing #linkedinads #linkedinagency #founderbranding #saas #b2bmarketing #demandgeneration #demandgen #content #b2b #revenue #contentmarketing #performancemarketing #videomarketing #personalbranding

Mike is a veteran of the Enterprise SaaS world:

- entered the software business in 1990

- was part of the internet boom as CMO of Versata, taking it public in 2000

- ran Wakesoft, Clarus Systems, and Instill Corporation as CEO

- "semi-retired" to join the boards of various software companies

- currently serving as President for LiftLab

I will dive into how Enterprise SaaS marketing has evolved, what it takes to win in today's world, how companies need to rethink their go-to-market, how to do hand-shake-trust-based business in a virtual-first world, and many more things.

Mike: https://www.linkedin.com/in/mkdevries/

LiftLab: https://www.liftlab.com/

Podcast: https://open.spotify.com/show/03CXzsZp7wdqIRVDcqPTFH

LinkedIn: https://www.linkedin.com/in/finnthormeier/

Website: https://www.project33.io/

#linkedin #founderledmarketing #linkedinads #linkedinagency #founderbranding #saas #b2bmarketing #demandgeneration #demandgen #content #b2b #revenue #contentmarketing #performancemarketing #videomarketing #personalbranding

How to Build a B2B SaaS in the Healthcare Space

Steven's Linkedin: https://www.linkedin.com/in/steven-charlap-md-mba-8911906/

SOAP Health: https://soap.health/

Website: https://www.project33.io/
Podcast: https://open.spotify.com/show/03CXzsZp7wdqIRVDcqPTFH?si=439e607dc707473a

LinkedIn (Finn): https://www.linkedin.com/in/finnthormeier/
LinkedIn (Jay): https://www.linkedin.com/in/jay-flores/
LinkedIn (Tobi): https://www.linkedin.com/in/tobias-moelenkamp/

#linkedinads #linkedinagency #linkedinadsagency #linkedinfounderbranding #saasmarketing #b2bmarketing #b2bcontent #demandgeneration #awareness #content #linkedin #b2b #revenue #contentmarketing #contentcreation #performancemarketing #videomarketing #inboundmarketing #personalbranding #founderledmarketing #contentstrategie #SMMA #contenttips

I chatted with Chris Walker about Founder-Led Marketing and how to run a successful CEO thought leadership program on LinkedIn in 2024.

In this episode we will cover:

• How Content Consumption Has Changed


• Outbound Sdr vs Thought


• Leadership Program


• How to Start Testing Founder-Led Marketing


• Founder-Led Marketing as a Category


• How to Start Driving Business Outcomes Through LinkedIn


• CEOs Crushing LinkedIn


• and many more topics
  

Chris Walker:

• LinkedIn: https://www.linkedin.com/in/chriswalker171/


• YouTube: https://www.youtube.com/ @ChrisWalker171 


• Podcast: https://podcasts.apple.com/us/podcast/b2b-revenue-vitals/id1511588213


• Refine Labs: refinelabs.com

Project 33:

Website: https://www.project33.io/
Podcast: https://open.spotify.com/show/03CXzsZp7wdqIRVDcqPTFH?si=439e607dc707473a

LinkedIn (Finn): https://www.linkedin.com/in/finnthormeier/
LinkedIn (Jay): https://www.linkedin.com/in/jay-flores/
LinkedIn (Tobi): https://www.linkedin.com/in/tobias-moelenkamp/

#linkedinads #linkedinagency #linkedinadsagency #linkedinfounderbranding #saasmarketing #b2bmarketing #b2bcontent #demandgeneration #awareness #content #linkedin #b2b #revenue #contentmarketing #contentcreation #performancemarketing #videomarketing #inboundmarketing #personalbranding #founderledmarketing #contentstrategie #SMMA #contenttips

Warmly, went from 0 to 100+ paying customers in 2023. More importantly, Maximus Greenwald (founder & CEO) went from founder-led sales to a repeatable sales process.

Here's how he built a repeatable sales motion this year (taken from Max's post, linked below):

Q1: Founder Led Sales

- Customers: 0-10- GTM Strategy: Design partners & founder friends

- Key experiment: messaging

Q2: Sales Leader Led, Founder Involved

- Customers: 10-30- GTM Strategy: Founder friends & startups, email sequencing

- Key experiment: LinkedIn sequencing

Q3: Seller-Led Sales, Founder Involved

- Customers: 30-60

- GTM Strategy: Omni-channel (LinkedIn/email), inbound (Warm Calling on the website with Warmly), territories

- Key experiment: Conferences

Q4: Seller Led, Sales Leader Run

- Customers: 60-100+

- GTM Strategy: No change from Q3 (repeatability!), just optimization

- Key experiment: LinkedIn social to drive inbound

We'll dive into:

- Key questions he asked himself at each stage

- Tools he implemented at every stage

- What did he hire for and when?

- Tips on implementing his framework

- How does he think about scaling from here on

Maximus Greenwald LinkedIn: https://www.linkedin.com/in/max-greenwald/
Warmly: https://www.warmly.ai/

Website: https://www.project33.io/
Podcast: https://open.spotify.com/show/03CXzsZp7wdqIRVDcqPTFH?si=439e607dc707473a

LinkedIn (Finn): https://www.linkedin.com/in/finnthormeier/
LinkedIn (Jay): https://www.linkedin.com/in/jay-flores/
LinkedIn (Tobi): https://www.linkedin.com/in/tobias-moelenkamp/

#linkedinads #linkedinagency #linkedinadsagency #linkedinfounderbranding #saasmarketing #b2bmarketing #b2bcontent #demandgeneration #awareness #content #linkedin #b2b #revenue #contentmarketing #contentcreation #performancemarketing #videomarketing #inboundmarketing #personalbranding #founderledmarketing #contentstrategie #SMMA #contenttips

Peter Caputa must be one of the most active software CEOs on Linkedin - and it's not for nothing.

After being VP of Sales at Hubspot, Peter joined Databox ($8M ARR b2b SaaS) in 2017 as CEO. And they are growing fast.

Peter Caputa: https://www.linkedin.com/in/pc4media/

Website: https://www.project33.io/
Podcast: https://open.spotify.com/show/03CXzsZp7wdqIRVDcqPTFH?si=439e607dc707473a


LinkedIn (Finn): https://www.linkedin.com/in/finnthormeier/
LinkedIn (Jay): https://www.linkedin.com/in/jay-flores/
LinkedIn (Tobi): https://www.linkedin.com/in/tobias-moelenkamp/

#linkedinads #linkedinagency #linkedinadsagency #linkedinfounderbranding #saasmarketing #b2bmarketing #b2bcontent #demandgeneration #awareness #content #linkedin #b2b #revenue #contentmarketing #contentcreation #performancemarketing #videomarketing #inboundmarketing #personalbranding #founderledmarketing #contentstrategie #SMMA #contenttips

Kevin Bobowski: https://www.linkedin.com/in/kevin-bobowski/

Website: https://www.project33.io/
Podcast: https://open.spotify.com/show/03CXzsZp7wdqIRVDcqPTFH?si=439e607dc707473a

LinkedIn (Finn): https://www.linkedin.com/in/finnthormeier/
LinkedIn (Jay): https://www.linkedin.com/in/jay-flores/
LinkedIn (Tobi): https://www.linkedin.com/in/tobias-moelenkamp/

#linkedinads #linkedinagency #linkedinadsagency #linkedinfounderbranding #saasmarketing #b2bmarketing #b2bcontent #demandgeneration #awareness #content #linkedin #b2b #revenue #contentmarketing #contentcreation #performancemarketing #videomarketing #inboundmarketing #personalbranding #founderledmarketing #contentstrategie #SMMA #contenttips